Sodium hydride → HCID 86672901, compound

HRID 1615375Notes

Reaction equation

HRID 1615375 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][NH:16]3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.[H-].[Na+]>CN(C=O)C>[Cl:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([N:16]2[C:17]3[C:13](=[CH:12][CH:11]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH:18]=3)[CH:14]=[CH:15]2)[CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 66955149HCID 66955149, compound

Product 1

HCID 86672901HCID 86672901, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3-Nitrophenyl)-1H-indole (2 g, 8.39 mmol) and 4,6-dichloropyrimidine (1.25 g, 8.39 mmol) were dissolved in DMF (20 mL) and sodium hydride (60% in mineral oil, 671 mg, 16.78 mmol) was added at 0° C. 1 hour later, ice was added to the reaction solution and the mixture solution was added to ice water. The mixture solution was stirred at room temperature for 12 hours. Thus prepared solid was filtered, washed with water, and dried in the air. 1-(6-Chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (2.61 g) was yielded as yellow solid.

Workup

  1. addition1 hour later, ice was added to the reaction solution
  2. filtrationThus prepared solid was filtered
  3. washwashed with water
  4. customdried in the air

Sources & evidence

ORD record
ord-38f1589f33694a32afe042be2aab2f1a
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

Loading…